Hydrochloric Acid → 1-phenylbut-3-yn-1-ol

HRID 259992Notes

Reaction equation

HRID 259992 reaction equation
Cl[C:2](=[CH2:12])[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].C[O-].[Na+].Cl>NCCCN>[C:6]1([CH:4]([CH2:3][C:2]#[CH:12])[OH:5])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 146636783-Chloro-1-phenyl-3-buten-1-ol

Product 1

HCID 110190061-phenylbut-3-yn-1-ol

Reagents, catalysts & solvents 1

HCID 4281,3-PropanediamineSolvent

Procedure

19.5 Grams of 2-chloroallylphenylcarbinol were dissolved in 100.0 g of 1,3-diaminopropane, and 9.2 g of sodium methylate were added. The mixture was allowed to react at 30° C. for 16 hours. Then, the reaction mixture was neutralized with concentrated hydrochloric acid, and insolubles were filtered off. The filtrate was concentrated under reduced pressure, and the resultant oily substance was purified by silica gel column chromatography to give 12.6 g of phenylpropargylcarbinol, nD20 =1.546, FI-MS m/e 146(M+), propargyl compound/allene compound=93.0/7.0.

Workup

  1. customto react at 30° C. for 16 hours
  2. filtrationwere filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fe059270fb6c44709b8d657c372ddeb7
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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